The Estate is Set to Auction in Cooperation with John Coles of Thomas & Talbot Estate Properties and Laura Farrell of TTR Sotheby’s International Realty

Oakendale Farm, an extraordinary estate in prestigious Virginia Hunt Country—a region known for its rolling hills, farmland, and equestrian culture—is heading to auction next month. Originally designed in 1938 by renowned architect William Lawrence Bottomley and crafted by master builder W. J. Hanback, the exceptional Colonial Revival stone manor will be offered in cooperation with John Coles of Thomas & Talbot Estate Properties and Laura Farrell of TTR Sotheby’s International Realty. Listed for US$19.6 million, starting bids are expected between US$5 million and US$9 million, with bidding for the property set to open on 16 January and conclude during a live auction in New York City  on 29 January.

Oakendale Farm epitomizes the quintessential Virginia Hunt Country lifestyle, capturing commanding views across the Bull Run to the Blue Ridge Mountains. The property entrance is from a quiet country road, just five minutes south of historic Middleburg, Virginia, providing a tranquil retreat while remaining close to local amenities.

The impressive interior of the manor house boasts wide, board walnut flooring throughout the formal living areas, a beautifully curved staircase in the foyer, and French doors leading out to the back gardens from the gracious living room. The library, with its handsome paneling, fireplace, and French doors to the gardens, offers an intimate setting for reading or relaxation. The elegant stone terrace, perfect for entertaining, features seating walls surrounded by boxwood gardens that draw the eye to the expansive views beyond. Additional highlights include a custom greenhouse, a five-bay garage with an upper-level entertainment room, a pool and pool house, and multiple dependencies such as a two-story office, guest house, and historic log cabin.

The second level of the manor house features a magnificent primary suite with a private porch for enjoying the glorious views, a sitting room, and two full baths. The remainder of this level offers three additional bedrooms, each with its own bath, as well as a two-bedroom suite with a sitting room and kitchenette, perfect for accommodating guests. This thoughtful layout provides ample space for both relaxation and entertaining.

“Oakendale Farm exemplifies Colonial Revival architecture at its finest,” said Coles. “The auction format provides an exceptional platform to connect this significant estate with buyers seeking both heritage and lifestyle—individuals who can truly appreciate the architectural pedigree and Virginia Hunt Country’s timeless appeal.”

In addition to the main manor, Oakendale Farm consists of two tax parcels—a 333.19-acre and 102-acre lot, both protected by an easement with the Virginia Outdoors Foundation. The preservation ensures the estate’s scenic beauty and historic integrity for generations to come.

“Oakendale Farm is an exceptional blend of historic architecture and modern luxury, set within one of Virginia’s most desirable locales,” said Farrell. “Its proximity to Middleburg and the Orange County Hunt territory makes it a haven for those who enjoy the outdoors and equestrian pursuits. This auction presents a unique opportunity for a new owner to acquire a piece of Virginia’s rich history, and we’re excited to display this to a global audience with Concierge Auctions.”

Virginia Hunt Country provides an unparalleled blend of natural beauty and historical charm. Middleburg, known as the nation’s horse and hunt capital, is just minutes away, offering excellent dining, boutique shopping, and cultural events. Outdoor enthusiasts will find themselves at home with access to hiking trails, equestrian facilities, and renowned horse shows. Nearby, the Blue Ridge Mountains offer endless opportunities for outdoor adventure and relaxation, from golf courses and vineyards to charming historic towns. For those seeking further amenities, Dulles International Airport is only a 45-minute drive, providing easy access to major cities along the East Coast. 

2227 Penny Lane is available for private showings by appointment, in person or virtually.